Porphyrins meso‐substituted with phenanthrene and 1,10‐phenanthroline

Abstract

Meso‐tetrakis(9‐phenanthryl)porphyrin and meso‐tetrakis(1,10‐phenanthrolin‐4‐yl)porphyrin were obtained and characterized by spectroscopy methods. The porphyrin containing phenanthroline substituents was formed with much smaller yield. It showed much slower progress of metallation with Cu(I) and Zn(II) ions than the phenanthreneporphyrin. While attachment of phenanthrene did not result in any meaningful changes in the uv vis spectrum when compared to other meso‐substituted tetraarylporphyrins (except that of [2.2]paracyclophanylporphyrin), the appearance of two N centers in each meso substituent substantially altered porphyrin absorption in the 530–600 nm region. Although the 1 H nmr 300 MHz spectra of both porphyrins showed the same deshielding of β‐pyrrole protons, the shielding of NH protons was more advanced in phenanthrolineporphyrin. Copyright © 1990 Journal of Heterocyclic Chemistry